Top MLB Christmas Week Moves: Blockbusters, Cy Young Signings Ranked

Sure, the holiday season can feel like a lull in the MLB offseason. But history? It tells a different story.

Some of baseball’s most defining free-agent signings and blockbuster trades have landed right around Christmas. While most fans are unwrapping gifts, teams quietly reshape their futures.

From megadeals that built contenders to contracts that became cautionary tales, Christmas week keeps showing up as one of the sport’s sneakiest turning points.

Yoshinobu Yamamoto and the New Standard for Holiday Blockbusters

December 2023 brought a new benchmark for Christmas-week deals. The Los Angeles Dodgers signed Yoshinobu Yamamoto to a 12-year, $325 million contract.

It wasn’t just a splash. It felt like a generational statement.

A Long-Term Bet on an Elite Arm

The Dodgers didn’t see Yamamoto as just a headline. They saw a championship-tested ace, polished in Japan’s NPB and on the international stage.

The length and size of the deal raised eyebrows. Still, for a franchise built on sustained contention, the logic made sense:

Clubs obsess over both performance and marketability these days. Yamamoto’s contract stands as a model of high-stakes, high-upside investment.

Barry Zito and the Dark Side of Holiday Spending

For every holiday home run, there’s a reminder that big checks don’t guarantee big returns. Enter Barry Zito and the San Francisco Giants.

A Contract That Never Matched the Hype

Back in 2006, the Giants handed Zito a seven-year, $126 million deal. It was one of the richest pitching contracts of its time.

On paper, they were getting a former Cy Young winner and durable lefty. On the field, they got just 6.5 WAR over seven seasons, a fraction of what that price tag implied.

Zito’s deal became synonymous with overpaying for past performance. It’s a reference point every time a mid-30s starter hits free agency.

The 1994 Padres Trade That Helped Spark a Pennant Run

Sometimes, the most important moves don’t feel seismic at the time. The 1994 trade that sent Steve Finley and Ken Caminiti to the San Diego Padres is a classic example.

How Finley and Caminiti Changed San Diego

In a multi-player deal, the Padres landed two cornerstone pieces: Finley, a dynamic center fielder, and Caminiti, a future NL MVP.

The payoff didn’t fully materialize until the late ’90s. By 1998, both were central to San Diego’s run to the World Series.

That trade shows how Christmas-week deals can be slow burns. Moves that look modest at first can end up reconfiguring a franchise’s identity.

The Greinke Trade: A Win-Win Holiday Blockbuster

Fast forward to 2010, and Christmas week gave us a rare win-win: Zack Greinke to the Milwaukee Brewers from the Kansas City Royals.

Cy Young-Caliber Ace for a Controllable Core

The Brewers added Greinke, a top-of-the-rotation force. For a small-market team, that’s huge—these guys rarely hit free agency.

He gave Milwaukee instant credibility and playoff-level firepower. The Royals, meanwhile, played the long game.

They received a package headlined by Lorenzo Cain and Alcides Escobar. Both became pillars of their 2014–15 pennant runs and 2015 World Series title.

This is one of those Christmas deals that reshaped not one, but two organizations’ futures.

Mark McGwire’s Extension: Keeping a Power Icon in Oakland

Not all impactful holiday moves involve changing uniforms. In 1992, the Oakland Athletics locked up Mark McGwire with a five-year, $28 million extension.

They kept one of the era’s premier sluggers in green and gold. McGwire’s deal stabilized an A’s lineup that had become synonymous with power and star quality.

A Franchise Face Stays Put

Though he would eventually be traded to St. Louis, this extension extended Oakland’s window with a hallmark middle-of-the-order bat. They didn’t lose him prematurely in free agency, which mattered for the franchise’s identity at the time.

Chris Sale to Atlanta: A Quiet Deal with Cy Young Results

Christmas week 2023 delivered another stealth move. The Atlanta Braves acquired Chris Sale from the Boston Red Sox.

At the time, it felt like a calculated gamble on a once-dominant lefty with an injury history. Atlanta’s bet paid off in spectacular fashion when Sale went on to win the 2024 NL Cy Young Award.

From Bounce-Back Candidate to Award Winner

For a Braves team already loaded with offensive firepower, turning a buy-low trade into an ace-level season? That’s the kind of opportunistic holiday deal that can swing a pennant race.

Mike Leake and the Template for Mid-Rotation Contracts

Not every Christmas signing is about star power. Some deals quietly define market tiers.

The St. Louis Cardinals’ five-year, $80 million pact with Mike Leake in 2015 did just that. Leake was never billed as an ace, but he was durable and dependable.

The Blueprint for “Solid, Not Spectacular” Starters

His contract became a template for mid-rotation arms. Teams still cite it when negotiating with innings-eaters in their late 20s and early 30s.

It wasn’t glamorous, but it was influential.

Short-Term Gains: Mike Hampton and Tim Raines Deliver

Two other notable Christmas-week moves delivered immediate impact, if not long-term franchise shifts. The Mets traded for Mike Hampton in 1999 and the White Sox acquired Tim Raines in 1990.

Short Windows, Big Returns

Hampton gave the Mets a frontline starter for their 2000 pennant run. He played a key role in taking New York to the World Series.

Raines, already a Hall of Fame-caliber talent, brought on-base skills, speed, and veteran presence to Chicago. He boosted the White Sox in the early ’90s.

Both moves show how teams sometimes use the holidays to capitalize on narrow contention windows, even if the relationship is brief.

Why Christmas Week Still Matters in MLB Front Offices

Take a look back at these deals and you’ll notice something: Christmas week isn’t just a pause button. It’s more like a pressure point for MLB front offices.

When the spotlight fades a bit, executives actually get the room to wrap up tricky negotiations. They spot chances to shake up their rosters, sometimes in ways that don’t even make headlines right away.

From Yamamoto’s record-breaking deal to Zito’s contract that still makes people wince, the holidays have a weird way of nudging teams into action. Some trades, like Finley and Caminiti, simmer for a while, while others—think Greinke, Hampton, or Sale—hit like a jolt.

 
Here is the source article for this story: A 12-player blockbuster? Cy Young signings? Ranking the biggest MLB Christmas week moves